it certainly is all about execution. most men wear their shorts too big and too long. this man's shorts look good on him because they are fitted (but not tight) and above the knee. this outfit is not sophisticated. is more about being comfortable and looking sharp. as "XO" said above, is all in the details (the strap of his wrist watch somewhat matching his belt). peace. sergio.

I usually dislike trad looks–they strike me as stuffy and boring. But somehow, this shows it to me in a new way. Maybe the right wrist band adds a little flair? Maybe the way his step seems springy? Maybe plain clothes let his natural handsomeness shine through? Whatever it is, he looks absolutely splendid. And I will consider preppy stuff with more care now!

yes, the rolled sleeves are key. i'm glad they are rolled and not neatly folded. his hair is tidy enough that he can have a little bit of casual feeling in there.

it's a little like how i style my husband – i make him shorts like these but about 3 inches shorter. men have wonderful legs and should show them off far more! i despise giant shorts down to mid-calf on so many north american men.

the boat shoes are a bit ubiquitous now – my husband has thse but in a brown leather – but i think that's okay, they're still great looking and it's so nice to see a man's bare ankle.

i know this is an american look, but it's also a little bit british, non?

yes, this look has been all over. my only 2 gripes are a) that deck shoes should always be a bit scuffed, to make one presume they're actually used for its intention rather than just show, and b) since this look has been harped to death, have the patience to add your own twist to it. in this scenario this look is followed to the T, void of any personality, save maybe the black band, which though arguable, isn't enough.

I'm a little surprised no one mentioned that his watch band cordinated very well with the belt. Nearly the same pattern but not. And the shoes, with thick white strips fro the laces and soles, mimic the same pattern. The thickness of the glasses (not to mention the thick band on the other wrist) brings all teh elements together. I'm not sure if all that is intentional though. I just noticed that is why the picture flows well.